Mike Massaro Flywire CEO

  • Flywire is a Boston-based payments company which has raised more than $143 million in VC funding.
  • The company makes international payments across healthcare and education simpler and recently raised $100 million to give it a valuation of around $700 million, according to PitchBook.
  • CEO Mike Massaro claims that changing his hiring approach has helped bring in better talent to the business.
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Hiring the best staff is one of the toughest parts of running a succesful business. Getting the right people with the best culture fit is a major cause of stress for founders. 

Beyond asking a set of generic questions to get responses, how do you get people who are the right culture fit for your company, particularly at an executive level?

Mike Massaro, CEO of Boston-based payments company Flywire, has his own way of dong things. “When I’m looking at working with an investor or trying to hire an executive I have a set of little tricks and tests I like to employ,” he told Business Insider in an interview. 

“Such as, how do they treat the wait staff if you’re at a dinner? Sometimes, I leave prospective candidates alone with my assistant in the meeting room and say i’m going to be late to see how they react to that and interact with her in that period.”

For Massaro, it’s important to ensure that potential staff behave as they would in a professional environment at that time. Unsurprisingly, a head of sales will probably sell themselves well at interview, but how do they interact with other staff members?

“Sometimes in the middle of a four hour interview session, I’ll say we’re having lunch with the team and then watch them to see whether they go first or last in line, whether they speak to people and interact with staff,” Massaro added. “It’s important that you have a culture fit.”

Massaro told Business Insider that his approach has helped hire team members who have been instrumental to the company’s recent successes. 

Flywire was founded in 2009 by Spanish entrepreneur Iker Marcaide, and was originally called peerTransfer. Massaro took over in 2013. The company handles billions in payments each year, having provided software to universities and healthcare providers to aggregate their payments processes.

While Massaro declined to give details on the firm’s valuation, data-firm PitchBook has said that the company secured $100 million in funding earlier this year to be valued at approximately $700 million with around $143 million in total financing.

This need for culture fit extends to getting the right investors on board too, according to Massaro. “It helps when boards understand the business because you need those people to be there when things are going wrong, not going well, and it’s the same with investors,” he said. 

SEE ALSO: This CEO has a pitch-deck slide titled ‘Why you shouldn’t invest in us’ that he says was a key draw for $140 million in VC funding

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The CEO of a 0 million startup explains why he's ditched the normal rules of hiring by leaving candidates with his assistant and taking them on team lunches


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